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Find cheap flights from Chicago Midway Airport to New York from $59

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to New York departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 6/21
Fri 6/28

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Best New York Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

New York
New York1 stop$106
Buffalo
Buffalo1 stop$159
Syracuse
Syracuse1 stop$168
Rochester
Rochester1 stop$208
Albany
Albany1 stop$236
Ithaca
Ithaca2 stops$343
Binghamton
Binghamton1 stop$399
Burlington
Burlington2 stops$342

Good to know

Low season

May

High season

October

Cheapest flight

$59
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago Midway Airport to New York LaGuardia Airport

FAQs - booking New York State flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to New York State?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to New York State.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to New York State?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to New York State from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to New York State?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to New York State with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to New York State?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to New York State from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to New York State

  • Morning departure is around 16% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to New York

 
Need help choosing which airline to fly with from Midway to New York? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10585 reviews
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

2.0 MediocreLisa, May 2024AUS - JFK
Read more about Delta reviews

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

It was a crowded flight. They did the best they could.

Boarding was great. The flight landed early. It took the crew over an hour and a half to bring out drinks. I paid to upgrade my seat to Comfort+ only to be near a crying/screaming baby who was seldom quiet. Noise-cancelling earbuds didn’t even help. Waste of money to upgrade.

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

They didn’t let me get my boarding pass through the app because I have a lap infant. The ticket said to see a gate agent but there was no gate agent available. I was supposed to go to the kiosk. Ended up missing my flight and they said that I never checked in to my flight so there was nothing that could be done. I will never fly spirit again. Not even worth the hassle and poor customer service.

I like strict carry on policy. Quick to board, quick to leave. Less time at gate and get there quicker

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

comfortable flight. not fond of the idea to pay for every little detail. baggage checkin or carry ons, basic snack, or some sort of basic entertainment/wifi. would be nice to offer these as perks and stop with the penny pinching.

Flight was delayed 2+ hours missed a concert because of it…

The seats were larger & more roomy than the old planes. the crew was excellent. . overall a very good flight.

No water for handwashing and they charged $5 for water. Spirit up-charges for every little thing and the planes themselves are old and nauseating.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Book cheap flights from Chicago to New York State

Recent round-trip flight deals

5/29Wed
1 stopFrontier
10h 10mMDW-LGA
6/1Sat
1 stopFrontier
13h 19mLGA-MDW
$106
6/5Wed
1 stopFrontier
9h 46mMDW-LGA
9/21Sat
1 stopFrontier
10h 53mLGA-MDW
$114
7/24Wed
1 stopDelta
5h 06mMDW-EWR
7/30Tue
1 stopDelta
5h 04mEWR-MDW
$188
6/6Thu
nonstopSouthwest
2h 05mMDW-LGA
6/7Fri
1 stopSouthwest
6h 05mLGA-MDW
$197
8/31Sat
1 stopDelta
3h 54mMDW-ROC
9/2Mon
1 stopDelta
3h 11mROC-MDW
$208
6/6Thu
nonstopSouthwest
2h 05mMDW-LGA
6/7Fri
nonstopSouthwest
2h 20mLGA-MDW
$237
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
7/15Mon
1 stopAllegiant Air
10h 22mEWR-MDW
$246
6/14Fri
1 stopAllegiant Air
10h 57mMDW-EWR
6/17Mon
1 stopAllegiant Air
10h 23mEWR-MDW
$261
5/31Fri
2 stops
16h 39mMDW-EWR
6/3Mon
1 stop
9h 48mEWR-MDW
$313
6/7Fri
1 stop
11h 31mMDW-EWR
6/10Mon
2 stops
14h 29mEWR-MDW
$331

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Recent one-way flight deals

6/5Wed
1 stopFrontier
9h 46mMDW-LGA
$59
5/29Wed
1 stopFrontier
10h 10mMDW-LGA
$63
8/7Wed
1 stopDelta
5h 19mMDW-EWR
$94
7/15Mon
1 stopDelta
5h 06mMDW-EWR
$97
6/14Fri
1 stopAllegiant Air
10h 57mMDW-EWR
$106
6/14Fri
1 stopAllegiant Air
10h 57mMDW-EWR
$109
5/30Thu
nonstopSouthwest
2h 10mMDW-LGA
$122
6/5Wed
1 stopSouthwest
6h 35mMDW-LGA
$131
6/8Sat
1 stopSpirit Airlines
13h 13mMDW-EWR
$173
5/29Wed
3 stopsSpirit Airlines
23h 14mMDW-EWR
$224

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Last minute flights from Midway to New York

Last minute flight, train and bus deals

5/25Sat
multi-stopFrontier
15h 55mMDW-LGA
5/31Fri
multi-stopFrontier
13h 23mLGA-MDW
$280
5/24Fri
multi-stopFrontier
10h 14mMDW-LGA
8/24Sat
multi-stopFrontier
6h 32mLGA-MDW
$284
5/24Fri
multi-stopDelta
7h 24mMDW-JFK
8/21Wed
multi-stopDelta
7h 22mJFK-MDW
$370
5/24Fri
multi-stopDelta
4h 37mMDW-EWR
6/8Sat
multi-stopDelta
3h 43mEWR-MDW
$371
5/27Mon
multi-stop
19h 49mMDW-EWR
6/3Mon
multi-stop
9h 48mEWR-MDW
$454
5/27Mon
multi-stop
19h 49mMDW-EWR
5/31Fri
multi-stop
9h 48mEWR-MDW
$540
5/25Sat
multi-stopPorter Airlines
6h 30mMDW-EWR
6/4Tue
multi-stopPorter Airlines
9h 27mEWR-MDW
$703
5/25Sat
multi-stopPorter Airlines
7h 30mMDW-EWR
6/4Tue
multi-stopPorter Airlines
10h 27mEWR-MDW
$708
5/24Fri
multi-stopWestJet
30h 03mMDW-HPN
5/27Mon
multi-stopWestJet
25h 38mHPN-MDW
$1,205
5/23Thu
multi-stopWestJet
21h 14mMDW-JFK
5/24Fri
multi-stopWestJet
20h 55mJFK-MDW
$2,499

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Chicago Midway Airport - New York State Flights